Kid-friendly holiday rentals in South Side
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in South Side
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side family-friendly rentals
Kid-friendly house rentals
Home in Chicago
4.95 out of 5 average rating, 128 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Home in Whiting
4.8 out of 5 average rating, 231 reviewsWhiting Getaway
Home in Chicago
4.98 out of 5 average rating, 322 reviewsCozy garden apartment historic Jackson Bvld.
Home in Wilmette
4.98 out of 5 average rating, 101 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Berwyn
4.91 out of 5 average rating, 263 reviewsPrivate apartment with retro vibe
Home in Chicago
4.95 out of 5 average rating, 179 reviewsParadise on the Park
Home in Manteno
4.98 out of 5 average rating, 121 reviewsUpdated, bright, and modern, 3 bedroom home.
Home in Chicago
4.97 out of 5 average rating, 362 reviewsTop Floor Escape | Modern Amenities | Lush Garden
Family-friendly apartment rentals
Rental unit in Chicago
4.85 out of 5 average rating, 169 reviewsYour brand new Chicago suite (unit 1F)
Rental unit in Chicago
4.89 out of 5 average rating, 250 reviewsModern
Rental unit in Chicago
4.99 out of 5 average rating, 150 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Rental unit in Chicago
4.89 out of 5 average rating, 303 reviewsVintage Bridgeport Apartment
Rental unit in Chicago
4.96 out of 5 average rating, 104 reviewsCute, Clean, Cozy Apartment in Pilsen
Rental unit in Chicago
4.84 out of 5 average rating, 178 reviewsLa Cottage
Rental unit in Chicago
4.91 out of 5 average rating, 118 reviewsModern 2BRD apartment| 5min to McCormick Place
Rental unit in Chicago
4.98 out of 5 average rating, 140 reviewsModern Apt with style & comfort in Pilsen Chicago
Family-friendly apartment rentals
Apartment in Chicago
4.9 out of 5 average rating, 104 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Apartment in Chicago
4.96 out of 5 average rating, 131 reviewsPrivate hot tub - King bed suite - Free parking
Apartment in Chicago
4.97 out of 5 average rating, 339 reviewsLincoln Square Gem!
Apartment in Chicago
4.86 out of 5 average rating, 140 reviewsThe En Bronze ~ 7mins To Dining & Downtown Chicago
Apartment in Chicago
4.97 out of 5 average rating, 109 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Apartment in Chicago
4.87 out of 5 average rating, 130 reviews3D Tour! Designer Condo near Logan Square
Apartment in Chicago
4.96 out of 5 average rating, 448 reviewsUnique Lincoln Park Duplex Apt
Apartment in Chicago
4.94 out of 5 average rating, 178 reviewsCharming Chinatown Home by McCormick★Downtown
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a fireplace South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Rentals with lake access South Side
- Rentals with pools South Side
- Rentals with breakfast South Side
- Family-friendly rentals South Side
- Smoking-friendly rentals South Side
- Flat rentals South Side
- Rentals with a firepit South Side
- Rentals with a hot tub South Side
- Rentals with beach access South Side
- Private suite rentals South Side
- Waterfront rentals South Side
- Monthly Rentals South Side
- Rentals with outdoor seating South Side
- House rentals South Side
- Rentals with an EV charger South Side
- Pet-friendly rentals South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Family-friendly rentals Milwaukee
- Family-friendly rentals Illinois
- Family-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom